Before becoming the global superstar she is today, Taylor Swift was just another aspiring country singer seeking her big break.
In a recent interview with Time magazine, she recounted a pivotal moment in her early career, a moment that wouldn't have happened without the kindness of fellow musician Kenny Chesney.
At 17, Swift was set to open for Chesney on his massive Flip-Flop Summer Tour, a chance that promised to catapult her career.
Unfortunately, the tour's beer sponsorship disqualified the underage Swift, crushing her dreams.
But fate had other plans. When she turned 18 in December 2007, Swift received a surprise birthday card from Chesney.
Inside, she found a check for an amount she described as "more money than I'd ever seen in my life."
This generous gift, Chesney's way of making up for the missed opportunity, allowed Swift to do something extraordinary: fuel her dreams.
She used the money to pay her band bonuses, cover tour bus costs, and invest in her artistic pursuit.
Chesney's belief in Swift wasn't just expressed financially.
He recognized her exceptional songwriting talent, saying, "She was a writer who had something to say...That isn't something you can fake by writing clichés. You can only live it, then write it as real as possible."
Their bond has grown over the years, translating into several memorable collaborations.
Chesney graced Swift's 2011 Speak Now World Tour, and Swift returned the favor by surprising him on the opening night of his 2015 The Big Revival Tour.
Their stage chemistry was undeniable, leading to their duet of "Big Star" being included on Chesney's 2017 live album.
Following Swift's Time magazine cover, Chesney took to social media to express his heartfelt congratulations.
He lauded her talent, saying, "Taylor, I knew looking in your eyes that first time on stage with us, you had 'it.' The hunger, that something special… A gift not everyone has to connect." He added, "I'm so proud of you & I love you."
Taylor, I knew looking in your eyes that first time on stage with us, you had “it.” The hunger, that something special… A gift not everyone has to connect. It’s been awesome watching you shine! Congratulations on being @TIME’s Person of the Year. I’m glad TIME sees what I’ve… pic.twitter.com/edlKvqRWQW
— Kenny Chesney (@kennychesney) December 6, 2023
